Metabolism of acetaminophen (paracetamol) in plants—two independent pathways result in the formation of a glutathione and a glucose conjugate View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2009-01-15

AUTHORS

Christian Huber, Bernadett Bartha, Rudolf Harpaintner, Peter Schröder

ABSTRACT

Background, aim, and scopePharmaceuticals and their metabolites are detected in the aquatic environment and our drinking water supplies. The need for high quality drinking water is one of the most challenging problems of our times, but still only little knowledge exists on the impact of these compounds on ecosystems, animals, and man. Biological waste water treatment in constructed wetlands is an effective and low-cost alternative, especially for the treatment of non-industrial, municipal waste water. In this situation, plants get in contact with pharmaceutical compounds and have to tackle their detoxification. The mechanisms for the detoxification of xenobiotics in plants are closely related to the mammalian system. An activation reaction (phase I) is followed by a conjugation (phase II) with hydrophilic molecules like glutathione or glucose. Phase III reactions can be summarized as storage, degradation, and transport of the xenobiotic conjugate. Until now, there is no information available on the fate of pharmaceuticals in plants. In this study, we want to investigate the fate and metabolism of N-acetyl-4-aminophenol (paracetamol) in plant tissues using the cell culture of Armoracia rusticana L. as a model system.Materials and methodsA hairy root culture of A. rusticana was treated with acetaminophen in a liquid culture. The formation and identification of metabolites over time were analyzed using HPLC-DAD and LC–MSn techniques.ResultsWith LC–MS technique, we were able to detect paracetamol and identify three of its metabolites in root cells of A. rusticana. Six hours after incubation with 1 mM of acetaminophen, the distribution of acetaminophen and related metabolites in the cells resulted in 18% paracetamol, 64% paracetamol–glucoside, 17% paracetamol glutathione, and 1% of the corresponding cysteine conjugate.DiscussionThe formation of two independently formed metabolites in plant root cells again revealed strong similarities between plant and mammalian detoxification systems. The detoxification mechanism of glucuronization in mammals is mirrored by glucosidation of xenobiotics in plants. Furthermore, in both systems, a glutathione conjugate is formed. Due to the existence of P450 enzymes in plants, the formation of the highly reactive NAPQI intermediate is possible.ConclusionsIn this study, we introduce the hairy root cell culture of A. rusticana L. as a suitable model system to study the fate of acetaminophen in plant tissues. Our first results point to the direction of plants being able to take up and detoxify the model substrate paracetamol. These first findings underline the great potential of using plants for waste water treatments in constructed wetlands.Recommendations and perspectivesThis very first study on the detoxification of a widely used antipyretic agent in plant tissues again shows the flexibility of plant detoxification systems and their potential in waste water treatment facilities. This study covers only the very first steps of acetaminophen detoxification in plants; still, there is no data on long-term exposure as well as the possible impact of pharmaceuticals on the plant health and stress defense. Long-term experiments need to be performed to follow the fate of acetaminophen in root and leaf cells in a whole plant system, and to evaluate possible usage of plants for the remediation of acetaminophen from waste water. More... »

PAGES

206

References to SciGraph publications

  • 2003-01-30. Arabidopsis glucosyltransferases with activities toward both endogenous and xenobiotic substrates in PLANTA
  • 2004. Metabolism of Natural and Xenobiotic Substrates by the Plant Glutathione S-Transferase Superfamily in MOLECULAR ECOTOXICOLOGY OF PLANTS
  • 1994. Sulfotransferase Enzymes in CONJUGATION—DECONJUGATION REACTIONS IN DRUG METABOLISM AND TOXICITY
  • 2005-01. Arzneimittel in der aquatischen Umwelt in ENVIRONMENTAL SCIENCES EUROPE
  • 2007-08. Humanpharmakawirkstoffe in der Umwelt: Einträge, Vorkommen und der Versuch einer Bestandsaufnahme in ENVIRONMENTAL SCIENCES EUROPE
  • 2007-11. Using phytoremediation technologies to upgrade waste water treatment in Europe in ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
  • 2006-06. Formation of glucoside conjugate of acetaminophen by fungi separated from soil in EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS
  • Identifiers

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    http://scigraph.springernature.com/pub.10.1007/s11356-008-0095-z

    DOI

    http://dx.doi.org/10.1007/s11356-008-0095-z

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1000223804

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/19145453


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    72 fate
    73 fate of acetaminophen
    74 fate of pharmaceuticals
    75 findings
    76 first finding
    77 first results
    78 first step
    79 first study
    80 flexibility
    81 formation
    82 glucose
    83 glucosidation
    84 glucuronization
    85 glutathione
    86 glutathione conjugates
    87 great potential
    88 hairy root cultures
    89 health
    90 high-quality drinking water
    91 hours
    92 hydrophilic molecules
    93 identification
    94 identification of metabolites
    95 impact
    96 incubation
    97 independent pathways
    98 information
    99 intermediates
    100 knowledge
    101 leaf cells
    102 liquid culture
    103 little knowledge
    104 long-term experiments
    105 long-term exposure
    106 low-cost alternative
    107 mammalian systems
    108 mammals
    109 materials
    110 mechanism
    111 men
    112 metabolism
    113 metabolism of acetaminophen
    114 metabolites
    115 model substrate
    116 model system
    117 molecules
    118 municipal waste water
    119 need
    120 paracetamol
    121 pathway
    122 pharmaceutical compounds
    123 pharmaceuticals
    124 plant health
    125 plant root cells
    126 plant systems
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    131 potential
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    133 quality drinking water
    134 reaction
    135 recommendations
    136 related metabolites
    137 remediation
    138 results
    139 root cells
    140 root cultures
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    142 similarity
    143 situation
    144 step
    145 storage
    146 stress defense
    147 strong similarities
    148 study
    149 substrate
    150 suitable model system
    151 supply
    152 system
    153 technique
    154 time
    155 tissue
    156 transport
    157 treatment
    158 treatment facilities
    159 usage
    160 waste water
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    163 water
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    167 wetlands
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